Popular Features
Sleeps
Sleeps
Destinations
Popular Cottages
- 2-Bedroom Cottage with Log Burner in Bakewell
- 2-Bedroom Barn with Log Burner in Earl Sterndale
- 1-Bedroom Pod in Kniveton
- 2-Bedroom House in Oker
- 1-Bedroom Cottage in Great Hucklow
- 2-Bedroom Barn in Ellastone
- 2-Bedroom Barn in Chesterfield
- 2-Bedroom Cottage in Youlgrave
- 2-Bedroom Cottage in Chinley
- Barlow Brook Cottage
- 3-Bedroom Cottage in Belper
- 1-Bedroom Apartment in Matlock
- Luxury 1-Bedroom Cottage in Ashford-in-the-Water
- 2-Bedroom Cottage in Holymoorside
- 2-Bedroom Cottage with Log Burner in Middleton-by-Youlgrave
- 2-Bedroom Cottage with Log Burner in Winster
- 2-Bedroom Cottage in Ashbourne
- 2-Bedroom Cottage in Winster
- 2-Bedroom Cottage in Barlow
- Dog-Friendly 2-Bedroom Cottage in Hayfield
- 1-Bedroom Cottage in Birchover
- 2-Bedroom Barn in Tansley
- 2-Bedroom Cottage with Log Burner in Ashbourne
- Dove 3-Bedroom Cottage with Log Burner in Bakewell
- 2-Bedroom Lodge in Stanton-by-Bridge
- 2-Bedroom Cottage with Log Burner in Castleton
- 3-Bedroom Cottage with Log Burner in Blackwell
- 2-Bedroom Cottage in Hayfield
- 2-Bedroom Mill in Tansley
- 1-Bedroom Mill in Bakewell
Winster Holiday Cottages
Our curated collection of Winster cottages has something for everyone... Whether you're idea of a great holiday is a modern glamping pod, or a rustic thatched cottage that's a hundred years old, we've got you covered! Each of our rentals features a private hot tub and everything you need for your next family holiday, romantic retreat or that getaway with a group of friends. Discover find your perfect Winster holiday home today.
Visitor Rating
4.5
- Grade II-listed cottage in Winster
- Wood burner and roof terrace
- King-size bedroom with window seat
- Village shop just yards away
- One dog welcome to stay
From £468 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Stone cottage in conservation village
- Wood burner and Smart TV lounge
- Sleeps 3 with flexible bedroom
- Enclosed garden welcomes two dogs
- Walking distance to Limestone Way
From £575 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Grade II listed 300-year-old cottage
- Woodburner in gritstone fireplace
- Walking distance to village amenities
- Garden with study room access
- Peak District location near Matlock
From £511 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Private enclosed woodland garden
- Wood burner lounge
- Peak District walking on doorstep
- One dog welcome
- 2 miles from Glossop
From £650 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Kinder Scout views from the door
- Private wildflower paddock
- Fire pit and summer house
- Designer glamping interior
- Direct train to Manchester
From £551 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4.6
- Panoramic Peak District countryside views
- Converted stone barn sleeping two
- Welcome up to three dogs
- Enclosed patio with outdoor dining
- Walking distance to local pub
From £638 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Log burner in cosy living room
- Up to three dogs welcome
- Walk to Torrs Gorge & Sett Valley Trail
- Enclosed private garden
- Secure lockable bike storage
From £433 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4.8
- Kinder Scout walks from door
- Wood burner and two sitting rooms
- King-size bedroom with en-suite shower
- Enclosed garden with Peak views
- Village location with pubs nearby
From £580 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Direct access to Kinder Scout trails
- Stone cottage sleeping three guests
- Open fire in lounge area
- Elevated garden with countryside views
- Two dogs welcome throughout cottage
From £417 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
3
- Adjacent to Kinder Scout path
- Spectacular Dark Peak views everywhere
- Wood burner in beamed lounge
- Sleeps four in two bedrooms
- Dog friendly walking paradise
From £484 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Four-storey townhouse sleeping six to eight
- Two dogs welcome with Peak walks
- Modern kitchen with dishwasher and utility
- Two separate living rooms across floors
- Near Bugsworth Basin and Lyme Park
From £570 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Two pubs one minute away
- Private garden and decking
- Walks to Kinder Scout from door
- Well-equipped kitchen and utility room
- Peak District on the doorstep
From £557 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4.6
- Two en suite double bedrooms
- Underfloor heating and wood burner
- Walks directly from the door
- Welcomes up to three dogs
- Peaceful end-of-lane converted coach house
From £575 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4.6
- Two en suite double bedrooms
- Underfloor heating throughout
- Wood burner and leather seating
- Welcomes up to 3 dogs
- Peak District countryside location
From £624 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4.6
- Part of Georgian mansion grounds
- Wood burner and flagstone floors
- Welcomes three dogs
- Extensive woodland walking routes
- Double with Juliet balcony views
From £575 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- 18th-century barn with countryside views
- Two en-suite bedrooms sleeping four
- Kitchen garden with organic produce
- Wood pellet heating and underfloor warmth
- Walking and cycling from doorstep
From £528 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Private hot tub in enclosed courtyard
- South-facing patio with Peak District views
- Dogs welcome up to three
- Alpaca walking experience on site
- Trails from the front door
From £1,590 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Stylish three-storey period property
- Sleeps six across three bedrooms
- Enclosed stone patio garden
- Minutes from Mam Tor and Kinder Scout
- Well-equipped kitchen with wine fridge
From £659 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Upside-down cottage with valley views
- Log burning stove and cosy sofas
- Walks from door across Peak moorland
- Two bathrooms including walk-in shower
- Sleeps four with two ground bedrooms
From £468 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Woodland setting with babbling stream
- Sleeps 4 in 2 bedrooms
- Wood burner and vaulted ceilings
- Kinder Scout on the doorstep
- Welcomes 2 dogs with parking
From £509 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Ground-floor barn conversion for two
- Welcomes two dogs to Peak District
- Floor-to-ceiling windows with tree views
- King-size bedroom with shower room
- Shared gardens with BBQ and stream
From £451 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Woodburner with logs provided
- Adjacent village pub dining
- Hillside walks from doorstep
- Two dogs welcome
- Countryside views from bedroom
From £428 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Sleeps 2 on working farm
- Wood burner with logs included
- Two bathrooms off bedroom
- Mountain bike secure storage
- Stunning Peak District countryside views
From £412 for 7 Nts
3-Bedroom Cottage in Bakewell
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- King-size four-poster bed
- Private garden with country views
- Stone cottage with gas stove
- Direct Peak District walking access
- One dog welcome
From £678 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Traditional Peak District barn conversion
- Stream-side garden with country views
- 1.2 miles from Castleton village
- Wood burner and freestanding bath
- One dog welcome
From £963 for 7 Nts
3-Bedroom Cottage in Bakewell
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- Secluded Peak District farmland location
- Mam Tor views from the terrace
- Wood burner for all seasons
- 0.5 miles from Castleton village
- On the Great Ridge walking route
From £619 for 7 Nts
3-Bedroom Cottage in Bakewell
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- 17th-century Peak District stone cottage
- Sleeps 4 in Castleton village
- Original beams and stone fireplace
- Parking for two cars on-site
- Steps from caverns and castle ruins
3-Bedroom Cottage in Bakewell
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Visitor Rating
4.4
- Former bakery with original features
- Sleeps 4 in two bedrooms
- Three-tiered garden with summer house
- Mam Tor views from top tier
- Central Castleton village location
From £543 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Walks directly from the cottage door
- Wood burner in stone fireplace
- Hope railway station in village
- Secluded courtyard garden with seating
- Recently renovated throughout
From £774 for 7 Nts
3-Bedroom Cottage in Bakewell
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Visitor Rating
4
- Sleeps 6 in Hope Valley
- Two dogs welcome with garden
- Three bedrooms in characterful cottage
- Walking distance to Hope village
- Pennine Way on the doorstep
From £569 for 7 Nts
3-Bedroom Cottage in Bakewell
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Explore more of Derbyshire
Popular towns and villages in and around Winster
Alfreton Ashbourne Bakewell Bamford Baslow Beeley Belper Bonsall Buxton Castleton Chatsworth Chellaston Chelmorton Chesterfield Chinley Clay Cross Cromford Darley Dale Denby Dronfield Edale Eyam Glossop Hadfield Hartington Hathersage Hayfield Heath Holmesfield Hulland Ward Kirk Ireton Kirk Langley Matlock Matlock Bath Over Haddon Somercotes South Wingfield Tansley Tideswell Tissington Whaley Bridge Wirksworth Youlgreave